Synthesis of Potential Phenolic Metabolites of Benzo[b]fluoranthene

Shantu Amin, Keith Huie, Hussain Nalb, George Balanikas, Stevens G. Carmella, Stephen S. Hecht

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Abstract

The syntheses of the 12 isomeric hydroxybenzo[b]fluoranthenes (hydroxy-BbF, 1–12) are described. 1-Hydroxy-BbF was prepared by treatment of 1-oxo-1,2,3,3a-tetrahydro-BbF (13) with Pd/C. 2-Hydroxy-BbF was synthesized by reduction of 13 with NaBH4, followed by dehydration, epoxidation, and treatment with Pd/C. 3-Hydroxy-BbF was obtained by reduction of 13 with Zn(Hg) followed by oxidation with Triton-B, dehydration, epoxidation, and aromatization. 4-Hydroxy-BbF and 7-hydroxy-BbF were prepared by reaction of ace-phenanthrylene with 1-acetoxybutadiene, aromatization, hydrolysis, and separation by HPLC. 5-Hydroxy-BbF was synthesized by reaction of o-bromobenzaldehyde with 3-methoxyfluorene, followed by cyclization with KOH and quinoline, hydrolysis, and purification by HPLC. 6-Hydroxy-BbF was obtained by regiospecific cyclization of 3-methoxy-11H-benzo[b]fluorene-11-propionic acid (33), followed by reduction, dehydration, aromatization, and hydrolysis. 8-Hydroxy-BbF was synthesized by dehydration of 7b,8-dihydro-7b,8-dihydroxy-BbF (39). 9-Hydroxy-BbF and 12-hydroxy-BbF were prepared by treatment of the corresponding oxotetrahydro-BbFs with Pd/C. 10-Hydroxy-BbF and 11-hydroxy-BbF were synthesized by reaction of fluorene with the appropriate bromomethoxybenzaldehyde followed by cyclization with hydrolysis.

Original languageEnglish (US)
Pages (from-to)1206-1211
Number of pages6
JournalJournal of Organic Chemistry
Volume51
Issue number8
DOIs
StatePublished - Apr 1 1986

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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    Amin, S., Huie, K., Nalb, H., Balanikas, G., Carmella, S. G., & Hecht, S. S. (1986). Synthesis of Potential Phenolic Metabolites of Benzo[b]fluoranthene. Journal of Organic Chemistry, 51(8), 1206-1211. https://doi.org/10.1021/jo00358a009